My experience has been the opposite. I jailbroke an iPhone 6s less than a year ago just by following the jailbreak du jour instructions. Any of my non-techy friends could have done the same.

Just a few months ago I tried to install an alternate rom on a Motorola Moto e6 and was dumbfounded by how impossibly complicated it seemed. Turns out this less than one year old phone had a locked boot loader and was not compatible with any modifications like I was attempting.

Every time I jailbreak my iPhone I always end up reverting it. Cydia is so janky and everything about the mods seem so tacky, tasteless, and janky I figure why bother. I need my phone to work.

Cydia is not very slick but it does its job and you don’t have to open it very often. (Perhaps it would be more accurate to say it’s about as slick as Synaptic.)

For everything else, it really depends on what you install. I think Colorflow, for instance, could very easily be mistaken for a native iOS feature.

Ah yeah, you gotta check bootloader lock status before buying. That's something that frosts me too, and it's why I pretty much only buy from OnePlus or Google.

If you buy a hack-friendly phone though, I've found it to be fairly easy to do, although I've always used CLI tools, so if someone (like non-techy friends) were to do it they'd probably be put off by the CLI.

Having used many iOS and android devices before, I usually preferred iOS devices because they were just far far more performant and snappier when running so jailbreaking was worth the inconvenience and it wasn't that hard. I remember trying out a samsung phone and the software they put on it was awful so I went straight back to an iphone at the time. But yes, it was annoying that I had to jail break it in the first place and that they kept trying to block it.

That being said, my current and last phone are the pixel 4a and 2 and they feel just as snappy as the iphones I haved used, I can install any software I want, and the 4a is really nice as it is only $350 with a fingerprint sensor and a headphone jack so I don't plan on going back to iOS any time soon.

For the majority of jailbreak users all they have to do is to use some program and you’re done. It’s simplified but as a user since 2010 that’s how I feel.

I don’t like android OS, and I like iPhones. I also like to tinker so I jailbreak.

I’d say it’s easy until you want to update. Hence how I’m still on iOS 12.

That’s kind if the nature of Jailbreak programs hooking into private functions though, and I don’t mind...

So would it be fair to say that the baseline phone is more important to you than the hackability, so you stick with iPhone, but if a jail break opportunity comes along then you will use it?

I grok that, makes sense :-)

Sounds about right. I’ve been jail broken more or less since 2012 though, with the exception of a couple of months last year.

I like iPhones as they are. They do many things I want from a phone well enough - except running sideloaded apps with Apple-exclusive entitlements. I find most Android phones annoying (suffering e.g. from poor palm rejection with borderless screens, touchscreen over-sensitivity, ads in system apps, piss-poor AAC encoding quality for Bluetooth audio, etc.)

As the old saying goes: some people want to do stuff with their phones, some people want to do stuff to their phones.

why is this downvoted? I think OP's question was honest.

I jailbreak because I prefer iOS over Android, and I enjoy using my phone as a PC sometimes. I also like themes, customizable app organization (like not having the standard homescreen grid), modifying my hosts file, and app modifications (like removing stories from Twitter)

This appeals to people for which Android isn’t an attractive platform.

I'm sorry, what what do you mean by "this?" What appeals to people for which Android is an attractive platform?

I'm specifically asking people who buy iOS devices and then want to jail break them why they aren't more attracted to an unlockable Android instead since they obviously don't like the restrictions that Apple puts in place.

Typo, sorry. I’m just saying that people jailbreak because they don’t want to use Android.

People want to hack on things. If they bought a superwidgetV2.X and the superwidget doesn't allow homebrew, people would hack the superwidget for homebrew. It's just how it is.

I totally agree, people want to hack on things. I love hacking on things. But I buy things that are specifically more hackable than other things to facilitate that desire.

Or are you saying they will hack on what they have, but don't like to enough to go out and find hackable things?

iPhones are arguably more privacy-friendly, since Apple services doesn’t harvest as much data as Google services.

i love free software, run linux on all my pc's etc, but i like having one computer that i don't have to worry about getting owned

I hear you, but if you're jail breaking your device aren't you opening yourself up to significant risk? You're using somebody else's exploit first of all, but then anything you install will have root on your device.

So I could see it if you were just buying an Apple device and leaving it alone, but if you're rooting I'm not sure I understand.

ah, i think i misunderstood the framing -- i do not jailbreak for that very reason, and i leave it to others to make the case!